


The Weirdest Night of His Life

by moodwriter



Category: Teen Wolf (TV)
Genre: Bottom Derek, Explicit Sexual Content, M/M, Other, Plot What Plot/Porn Without Plot, Rape/Non-con Elements, Tentacle Monsters, Tentacle Rape, Tentacles
Language: English
Status: Completed
Published: 2014-06-29
Updated: 2014-06-29
Packaged: 2018-02-06 18:13:14
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 3,584
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1867560
Author URL: https://archiveofourown.org/users/moodwriter/pseuds/moodwriter
Summary: <blockquote class="userstuff">
              <p>When a monster makes Derek its play thing Stiles talks him through it.</p>
            </blockquote>





	The Weirdest Night of His Life

**Author's Note:**

> I probably should apologize, but then again, you don't have to read if you don't like the genre. :) I've warned. It's nothing but porn, but it has feelings, too, because I'm a sucker for feelings. It's weird, it's pure fantasy, and it's meant to be enjoyed by the curious few who happen to like tentacles. :) 
> 
> I might be one of them. If I dare to admit. Sometimes. On rare occasions. Right now, I'm procrastinating like hell so tentacles happened. So yeah, blame university. 
> 
> This was betaed by the wonderful @leela_cat who always pokes at things that I haven't even thought about. It's both incredibly amazing and forever humbling because I do realize how little I know of this craft still. 
> 
> Thank you so much for reading the warnings and not reading something you don't want to read. :) The rest of you, enjoy and have fun! :D

Stiles gets a phone call in the middle of the night, and that’s how the weirdest night of his life begins. 

Scott tells him to meet the pack outside Derek’s loft, but gives him no details about why. 

Stiles sneaks out, drives off, and gets there as fast as he can because Scott sounded like it was urgent. 

Besides, it’s always something bad. It’s them after all. 

“What is it?” Stiles asks, falling out of the Jeep, barely staying on his feet. 

Scott looks at him, the rest of the pack crowding behind him. “Derek… is in trouble.”

Of course Derek’s in trouble. When isn't he? “Then why aren’t you helping him? Is he there?” Stiles points at the tall building and its top floor. 

“He’s there, but we can’t go in. We’ve tried.”

Stiles stares at them — Kira's worried expression, Malia's strange excitement, Lydia's cool stare — and he wonders what's really going on. "What's happening to him?"

Scott winces visibly. "We're not sure. I just know something has him, and if we go too near, it starts to strangle him."

"Then why didn't you call me earlier? Everyone else is here."

Kira bites her lip, then says, "He specifically asked not to call you." She looks Stiles directly in the eyes and whispers, "Sorry," like it's her fault in any way. 

Stiles breathes in and out a few times, trying to calm himself. It's difficult because things like this make him feel left out. He tries to believe that they trust him, that they think he can handle himself in a fight, but whenever something like this happens, Stiles becomes doubtful. He hates to be insecure. It's the worst feeling in the world. 

Scott pats Stiles' arm. "He's ashamed of the whole thing. He doesn't want you to see him like this."

"Like what?"

"We don't know. The moment we try to get in Derek stops us because the creature hurts him. You're his last hope."

"And he really didn't want me to be." Stiles sighs. 

"Well... yeah..." Scott looks bashful. "But he needs you so please try to help him."

Stiles heads for the front door, turning to look at Scott once more. "I should probably call him, huh?"

"Yes. And Stiles, if you need anything, we're here." 

Stiles nods, walking fast, entering the building and almost running toward the elevator. Once he's there, he calls Derek, waits for him to answer, pacing the small space impatiently. 

"Hi," Derek says, sounding reluctant and pissed off. 

"What's your problem?"

Derek is quiet, then mutters, "I'm trapped."

"By what?" Stiles tries to breathe normally, but he's getting anxious. 

"A monster."

"I figured that. What kind of a monster? What do you need? And how can I help?" Stiles has no superpowers. He's not the best option for this rescue mission. Yet, he always seems to be at the center of things. 

"If you can get through the door, you'll know. We'll figure out what to do if that happens."

Sometimes Stiles hates Derek. Almost all the time, if he's honest. "How did you become a monster play thing?"

Derek chokes on something, coughing, and when he speaks, he sounds weirder than before. "It was here when I woke up. I didn't go looking for trouble."

Stiles laughs quietly as he reaches Derek's floor. "You never do. Okay, I'm here. How far did the others get?"

"Not this far. You don't seem to scare it."

Stiles feels extra manly after that. He reaches Derek's door, turns the key slowly, waiting. "Anything?" he asks and when Derek says everything's fine, Stiles pulls the door open. 

He can't see properly in the darkness of the loft, but there is definitely something on Derek's bed, and it's holding Derek in its clutches. It's a huge shadow, covering most of the wall and ceiling above the bed, and Stiles is freaking terrified. "What am I supposed to do?"

"It says it's not going to kill me if you come here," Derek says, his voice raspy but still strong.

"Is it talking to you telepathically?" Stiles asks, staring, his mouth falling open when he stalks closer. 

Derek is lying on his back, one of his hands pulled over his head, captured in slime that's oozing from the creature’s body, and the other still clutching his phone desperately. Derek is shirtless, but he has his sleep pants on, and there are tentacles wrapped around his upper body, one circling his throat, too. 

When Derek doesn't say anything, Stiles repeats the question. 

Derek just stares at him, his eyes huge. 

"Those are tentacles," Stiles says helpfully, and Derek growls at him, but that isn't a wise thing to do because the tentacle around Derek's throat tightens, squeezes, makes him lose his breath. Stiles panics, moving closer still, not thinking at all. "Please don't hurt him."

When the monster loosens its hold on Derek, parts of Stiles' brain start to operate properly again and he examines all the remnants of tentacles on the bed and on the floor. Derek put up a fight before he gave in. "What do you want from us?" he asks, trying to be as non-threatening as possible. 

The room is so quiet it feels like time stands still, then three of the tentacles move lower down Derek's body, two of them wrapping around his thighs, spreading them wide, and the third one sliding under the waistband of his sleep pants. 

"No, no, no..." Derek says, the words like bullets hitting Stiles. "Make it stop."

Stiles moves without thinking again, grabbing the tentacle slithering inside Derek's pants and pulling it out. It wiggles against his hold, wraps around his arm, and holds onto him. It's strong, stronger than Stiles thought. "Hey, listen, there's no consent here. You can't do that to someone against their will." He's just spouting words, trying to find the creature's face. Maybe he can talk some sense into it. If he can't, this is going to turn into bad porn, the kind that has a sticky ending. "Are you listening to me?"

"It's listening," Derek says slowly. "And it doesn't understand you. It's a chaos demon, Stiles. It doesn't care." Derek tries to wiggle free, but only ends up with more tentacles wrapping around him, one hovering dangerously close to his mouth. Stiles grabs that one too because Derek is his only connection to the demon, and he needs to be able to hear Derek’s words. And he doesn’t want anything penetrating Derek in any way. It’s a fierce feeling, and it scares him a little. 

"What can I do?" Stiles asks, staring at the tentacle in his right hand, the one he captured last. It’s dark gray and blue with a lizard-like skin, and it’s warm to the touch. It’s also slippery and slimy, and Stiles knows exactly why. They have been trapped inside a tentacle porn movie. 

“I don’t know,” Derek says, finally dropping his phone, grabbing one of the tentacles touching his chest, and throwing it far away from himself. “I don’t fucking know. Talk to it. It seems to like your voice.”

“Has it tried anything… inappropriate?” 

Derek snorts, closing his eyes. “It’s very interested in all the orifices of my body, but no, not yet.”

Stiles sighs. Okay, he can do this. He can reason with a tentacle monster. “Hello, hi… How are you?” 

Derek rolls his eyes, groaning.

“Shut it. I’m trying.” Stiles looks at the monster again. “I’m Stiles. This is Derek. We would very much like to get out of here. Would you mind if we left? We could just pretend this never happened.”

The tentacle around Stiles’ left arm tugs him closer, and Stiles loses his balance, falling against the massive body of the monster. “Hey, hey, I’m not your play thing and neither is Derek. We’re people, and we don’t agree with this. A strict no sex rule here, okay?”

“Stiles, it wants you to watch. It’ll let us go if you watch.”

“Watch what?” Stiles says, panicking again. He pushes himself off of the monster, staring down at Derek. “Talk to me!”

“It won’t kill me if you sit in that chair and let it do what it wants.” Derek sounds resigned, pointing at the chair at the end of the bed. 

“No fucking way,” Stiles breathes out. “No way.”

There are two tentacles around Derek’s throat now, squeezing, and Derek is gagging for air, clawing at the tentacles with his free hand. It’s futile, and soon, that hand is captured too, and Derek is helpless. Stiles tries to help him, tries to free Derek from their hold, screaming at the beast, “Don’t hurt him. You have no idea what he’s been through. Please? You can have me, just don’t hurt him.”

Derek’s eyes go wide, and he tries to shake his head. Stiles ignores him, pushing his hand between the tentacles and Derek’s throat, attempting to give him enough room to breathe. It helps, and Derek takes a shuddering breath, coughing. 

“Let him watch if you need someone to watch. I can do this. Please?”

Derek growls, then croaks, his voice mostly gone, “I can’t live with myself if you do this.”

Stiles looks at him. “You’ve been through enough abuse.”

“Like you haven’t.” 

The monster makes the decision for them, lifting Stiles up and sitting him in the chair, leaving the two longest tentacles to hold him there. Stiles screams at it mindlessly, and when he does one tentacle enters his mouth, oozing some kind of liquid that makes him relax. He’s furious, but his body can’t do anything, and soon, even his mind mellows down a bit. When it does, the tentacle leaves and goes to Derek instead. 

Stiles stares at Derek, who leans against the monster, resting there like he has no worries in the world. Stiles can see how tense his spine is, though. 

“Derek?” He can barely speak. 

“I’m okay. I’m okay.” Derek closes his eyes and opens his mouth, letting the monster feed him the aphrodisiac. It looks obscene, and it isn’t over as quickly as it was with Stiles. Derek is a werewolf, and he needs to be more relaxed than Stiles. That thought makes Stiles fight against his restraints. He never agreed to this. They should’ve had a plan B. Or even a plan A. 

The tentacle fucks Derek’s mouth until his lips are swollen and his jaw stiff and probably aching. It’s not something Stiles wants to see, but if Derek’s life depends on him watching this then he will watch every second of it, no matter how awful it becomes. 

“Stiles,” Derek whispers, his voice hoarse. He sounds out of it already and his body is undulating against the mattress, like he can’t control any needs his body might have. Stiles hates the monster, but he’s glad that it’s not going to be violent. Or at least, he hopes it won’t be. 

“I’m here.”

“It’s going to fuck me,” Derek says, then bites his lip like he’s ashamed of the words. His eyes are still closed. 

“I know.”

“I’ve never been fucked.” Derek sounds scared. 

Stiles’ breath catches. “Just… relax. It’s easier if you relax.”

Derek tenses because five tentacles remove his clothes gently, lifting his ass up and holding his legs as they pull the sleep pants and boxers off. “I can’t relax,” Derek says, groaning when the tentacles wrap around his legs and pull them wide apart again. 

Stiles can see everything: Derek’s cock lying heavily on his stomach, his balls, and the tiny hole Stiles would like to touch himself. He desperately wants to cover it now, though, wants to protect Derek from this. “You’re doing fine,” Stiles whispers, choking on the word fine. 

“Liar.” Derek tries to free himself, tries to pull his hands out of the slime that’s holding him captive, but it’s not happening. Nothing is going their way tonight. 

“I’d like to do that to you,” Stiles says because he has to say something, has to help Derek through this. “Spread you on the bed and lick you open. I’d be so careful with you.”

Derek opens his eyes, looking bewildered. “What?”

“Would you like that?” Stiles is not bold; he’s desperate. Derek is stiff as a brick, and he’s going to get hurt like that. 

Two tentacles wrap around Derek’s cock, and one starts to massage his opening, making him wet, looser, easier to access. 

“I’d kiss you everywhere. I’d take my time with you. I don’t think anyone’s ever worshipped that body of yours enough, but it’s not why… The why of the matter lies elsewhere. You deserve to be pampered. And I’d love to be the one to give you the best orgasms you’ve ever had.”

“Stiles, your mouth…” Derek’s voice is gone because the two tentacles have managed to make him hard and the third one has made him so wet he’s leaking, the sheets damp with it.

“You like my mouth, don’t you? My mouth could do amazing things to you. My mouth would love to suck your cock.”

Derek groans, and not just because there’s a tentacle at his entrance, moving around the puckered hole and then pushing in slowly. It’s agonizingly slow, actually, and Stiles can’t say anything, no matter how much he wants to. Derek is being penetrated by a monster and nothing that’s ever happened to them can beat that. “Stiles… talk to me. Plea--se.”

Stiles clears his throat, tries to think of something, anything to say, but there’s nothing. He can only watch. The tentacle goes deeper than should be possible, and Stiles can see it push against the skin of Derek’s stomach. It has to hurt; it’s not small. 

“And if you liked…” Stiles finally says, “I’d fuck you so slowly. I’d make it so good. You’d be completely open for me because I’d use hours to prepare you. No amount of lube would be enough, and you’d be so spent already that riding my cock would be impossible. I’d have to lay you down on the bed and spread your legs with my knees and sink into you. Would you like that?”

Derek lets out a litany of profanities. “Yes, fuck. Yes.”

The tentacle stops its movement, stays still for a while, and then pumps Derek full of its seed. Some of it spills out when the tentacle exits, and when it does, Derek cries out, curling in the hold of the tentacles. 

“Is it over?” Derek asks, and he sounds so exhausted Stiles feels sorry for him. It’s nowhere near over. There’s a line of tentacles ready to fuck Derek. 

“Not yet, baby. Hang in there.”

When the next one enters Derek it’s somehow harsher, more eager to just satisfy its own need, and Derek squeezes his eyes shut, gritting his teeth. It’s over faster, too, and maybe that’s better. 

The next one is a pair, one entering Derek’s mouth and one his ass, their movements synchronized. It’s terrible and fascinating at the same time, and Stiles hates his scientific mind. Sometimes he wishes he could be like everyone else. 

He’s getting hard watching his friend writhe in the clutches of dozens of tentacles. He hopes it’s the aphrodisiac that’s causing it. He can’t face his friends if it isn’t.

Then the tentacle in Derek’s mouth pulses come down Derek’s throat, making him swallow it, and all Stiles can think about is Derek’s throat working all of it down, swallowing, swallowing, swallowing, and then the tentacle is gone, leaving Derek breathless.

Derek wails, shaking, sounding like he’s in pain, and for a second, Stiles thinks he’s going to die, but then Derek’s cock spurts come, the tentacles milking him as long as it takes to get every last drop out of him. They gather it carefully away, and then leave his cock alone. 

The weirdest thing is that after that, Derek isn’t just being fucked; he’s fucking himself on the tentacle, his hips moving in tandem with its thrusts. His cheeks are flushed, and Stiles knows he’s still aware of what he’s doing, but can’t stop himself. 

“I’d never make you feel ashamed for wanting more,” Stiles says, his voice deep and full of lust he can’t hide. 

Derek groans. “Shut up, Stiles.”

“I thought you liked it when I talk.” He tries to be teasing, but it falls flat. He wants to help Derek so badly. 

Derek doesn’t say anything, just turns his head from side to side, mad with lust. The orgasm didn’t seem to help him at all. 

Then the tentacle in Derek’s ass stills, spurts come into Derek, pulls out with a wet sound, and moves out of the way when other two are ready to take its place. They drill inside Derek, moving in circles, stretching him wide open, and Derek arches his back, screaming. 

“Hey, hey, you’ll be fine. I promise,” Stiles says softly, trying to reach Derek’s rational mind again, but it’s impossible. Derek is too far gone. There’s nothing more left but screams and whines and growls, and the jerking of his hips. 

The two tentacles inside Derek move to the sides of his hole, giving room for a bigger one that’s waiting right above Derek’s hole, ready to plunge in. When it does, Derek shifts, his beta face hiding most of the pain, but his scream showing all of it. 

It’s brutal and quick, and it’s over so soon Stiles feels dizzy when the huge tentacle releases its load, filling Derek, making his stomach taut with the monster’s seed. 

When it’s done, when it’s over, the monster pulls out of Derek slowly, releases his arms and legs, pats his cheek, cock, and ass, and then vanishes into thin air.

Stiles runs to Derek the moment he’s freed. Derek is curled up in a ball, hiding his face, shaking. 

“Hey, hey, you’re fine. You survived.” Stiles grabs Derek’s shoulder, tries to make Derek look at him. “I promised to be good to you. I will be.”

Derek snarls, still in his beta form, more wolf than human right now. His eyes are blue when he stares at Stiles. 

“Let’s get you to the shower, okay, big guy?” Stiles pulls at Derek, helps him up, and together they walk to Derek’s bathroom. Stiles doesn’t say anything about the line of come they leave behind.

In the bathroom, he helps Derek into the bathtub, makes him sit down, and starts washing him. He cleans Derek all over, noticing that there are no visible wounds on Derek’s body, that he’s entirely healed already. 

Once he’s done washing Derek, he fills the tub with water, adds bath oil and bubbles, and tells Derek to lean back, relax and not think about anything. 

Stiles is trying not to think, too. Derek is his main concern, and besides, Stiles prefers to ignore things until they go away. This is definitely one of those things he’s filing under _too scary to deal with until ten years has passed_. 

When he’s sure Derek won’t drown himself or do something else equally stupid, Stiles goes back to Derek’s sleeping alcove, removes the dirty sheets, throws them into a trash bag, and then puts new ones on the bed. Next, he cleans the floor, opens the window, and once he’s satisfied with everything he goes downstairs and tells the pack to fuck off, that he’s going to take care of Derek and they are not needed right now. He does it gently even though he has very little patience with them and their questions. He’s never going to tell them anything unless Derek wants to share it with them. 

All that done, he goes back to the bathroom. Derek is still lying in the bathtub, his eyes closed. 

“How are you?” Stiles asks, hoping his voice is as soft as he wants it to be. 

“I would’ve died without you.”

The words startle him because somehow he thought Derek would still be less human. “I wish I could’ve done more.”

“You did plenty.” Derek turns to look at Stiles. “Nobody else could’ve done what you did.”

“What did I do?” Stiles sits on the toilet seat, watching Derek intently. 

“I wasn’t scared because of you. I wasn’t ashamed because of you.”

“You have nothing to be ashamed of,” Stiles says vehemently. “It could’ve easily been me. It happened. It’s not your fault.”

Derek smiles. “I know. And you made it clear with everything you said and how you said it.”

Stiles doesn’t know what to say. He rarely feels like he manages to do something right. Usually he’s fumbling in the dark. “I’m glad I was here. I wish I could’ve stopped it. But I’m glad I was here.”

Derek holds his hand out, and Stiles takes it. “Thank you,” Derek says. 

It’s one of those things Stiles could’ve never predicted: how much he’d fall for Derek. How much he doesn’t hate him. How much he wishes he could save Derek from his past. It’s not possible, though, and that’s why, instead, he’s going to accept Derek with all the parts of his past. “I kind of dig you,” he says carelessly.

Derek laughs, the sound so unexpected Stiles laughs with him. “I dig you back,” Derek says, his expression ridiculously insecure, and Stiles launches himself at Derek, projectile hugging him and sending water everywhere in the bathroom. He doesn’t care. He can’t save Derek, but he can be good to him. That’s something.


End file.
